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  • Title: Regiodivergent synthesis of trisubstituted furans through Tf(2)O-catalyzed Friedel-Crafts acylation: a tool for access to tetrahydrofuran lignan analogues.
    Author: Comegna D, DellaGreca M, Rosaria Iesce M, Previtera L, Zarrelli A, Zuppolini S.
    Journal: Org Biomol Chem; 2012 Feb 14; 10(6):1219-24. PubMed ID: 22179391.
    Abstract:
    3- or 4-Aroylfurans have been prepared selectively and in high yields from a common precursor by simple tuning of reaction conditions in Friedel-Crafts acylation promoted by triflic anhydride. The formation of products can be explained on the basis of the ring-chain tautomerism occurring in compounds equipped with two neighbouring carboxylic functions. Since 4-aroylfuran derivatives show a typical lignan backbone, suitable hydrogenation conditions were found out to gain tetrahydrofuran lignans.
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